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(1R,3S,3aR,8bS)-3a-(1,3-benzodioxol-5-yl)-6,8,8b-trimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1-ol

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID cf0f28e6-c282-44bc-8b1f-699b44422b70
Taxonomy Organoheterocyclic compounds > Benzofurans > Flavaglines
IUPAC Name (1R,3S,3aR,8bS)-3a-(1,3-benzodioxol-5-yl)-6,8,8b-trimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1-ol
SMILES (Canonical) COC1=CC2=C(C(=C1)OC)C3(C(CC(C3(O2)C4=CC5=C(C=C4)OCO5)C6=CC=CC=C6)O)OC
SMILES (Isomeric) COC1=CC2=C(C(=C1)OC)[C@@]3([C@@H](C[C@H]([C@@]3(O2)C4=CC5=C(C=C4)OCO5)C6=CC=CC=C6)O)OC
InChI InChI=1S/C27H26O7/c1-29-18-12-22(30-2)25-23(13-18)34-26(17-9-10-20-21(11-17)33-15-32-20)19(16-7-5-4-6-8-16)14-24(28)27(25,26)31-3/h4-13,19,24,28H,14-15H2,1-3H3/t19-,24+,26-,27+/m0/s1
InChI Key SKVASQVJEVFEOC-KTWRFPGGSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H26O7
Molecular Weight 462.50 g/mol
Exact Mass 462.16785316 g/mol
Topological Polar Surface Area (TPSA) 75.60 Ų
XlogP 3.50
Atomic LogP (AlogP) 4.11
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,3S,3aR,8bS)-3a-(1,3-benzodioxol-5-yl)-6,8,8b-trimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1-ol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9829 98.29%
Caco-2 + 0.5660 56.60%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.6468 64.68%
OATP2B1 inhibitior - 0.8656 86.56%
OATP1B1 inhibitior + 0.8847 88.47%
OATP1B3 inhibitior + 0.9161 91.61%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.9697 96.97%
P-glycoprotein inhibitior + 0.8737 87.37%
P-glycoprotein substrate - 0.6777 67.77%
CYP3A4 substrate + 0.6111 61.11%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate + 0.4301 43.01%
CYP3A4 inhibition + 0.7352 73.52%
CYP2C9 inhibition - 0.5525 55.25%
CYP2C19 inhibition - 0.6513 65.13%
CYP2D6 inhibition - 0.8001 80.01%
CYP1A2 inhibition - 0.8112 81.12%
CYP2C8 inhibition + 0.6310 63.10%
CYP inhibitory promiscuity + 0.6035 60.35%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9408 94.08%
Carcinogenicity (trinary) Non-required 0.3509 35.09%
Eye corrosion - 0.9922 99.22%
Eye irritation - 0.9074 90.74%
Skin irritation - 0.8014 80.14%
Skin corrosion - 0.9551 95.51%
Ames mutagenesis + 0.5330 53.30%
Human Ether-a-go-go-Related Gene inhibition + 0.7344 73.44%
Micronuclear + 0.6700 67.00%
Hepatotoxicity - 0.5250 52.50%
skin sensitisation - 0.8011 80.11%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity - 0.5000 50.00%
Nephrotoxicity - 0.6201 62.01%
Acute Oral Toxicity (c) III 0.4848 48.48%
Estrogen receptor binding + 0.8886 88.86%
Androgen receptor binding + 0.7948 79.48%
Thyroid receptor binding + 0.7870 78.70%
Glucocorticoid receptor binding + 0.8473 84.73%
Aromatase binding + 0.6214 62.14%
PPAR gamma + 0.7676 76.76%
Honey bee toxicity - 0.8052 80.52%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.5151 51.51%
Fish aquatic toxicity + 0.8556 85.56%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.68% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.85% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.71% 96.09%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 96.28% 89.44%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.07% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.73% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.26% 86.33%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 91.74% 92.62%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 89.52% 96.77%
CHEMBL240 Q12809 HERG 89.22% 89.76%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 88.93% 95.50%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 88.36% 94.08%
CHEMBL4306 P22460 Voltage-gated potassium channel subunit Kv1.5 87.31% 94.03%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.30% 97.14%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 84.75% 94.80%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 84.28% 96.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.97% 95.89%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.05% 94.45%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 82.72% 94.62%
CHEMBL4145 Q9UKV0 Histone deacetylase 9 82.60% 85.49%
CHEMBL4208 P20618 Proteasome component C5 82.52% 90.00%
CHEMBL2581 P07339 Cathepsin D 81.04% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.79% 94.00%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 80.00% 100.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Aglaia perviridis

Cross-Links

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PubChem 71658107
NPASS NPC164152
ChEMBL CHEMBL2332221
LOTUS LTS0218631
wikiData Q105255061